Why you should care

“Our dreams are young and we both know / They’ll take us where we want to go,” the young Hawaiian crooned while staring into the eyes of a pretty blonde. Glenn Medeiros was just 16 when he offered up his rendition of George Benson’s “Nothing’s Gonna Change My Love for You” in a local song contest on Kauai, propelling himself to international stardom.

Perhaps the optimistic lyrics rang true for the young heartthrob back in the age of Ferris Bueller, popped collars and indulgent love songs. The curly-haired Karate Kid look-alike’s synth-filled cover became a wedding staple when it hit the charts in 1988. While initially hailed as a ballad singer, Medeiros was soon pushed, uncomfortably, into other genres, which ultimately saw him trade in his big hair and leather pants for suits, ties and a career in education. And much like those who once owned parachute pants, he’s not missing much about his ’80s heyday.

I didn’t see myself being able to be successful anymore as a singer in [that] kind of environment.

Glenn Medeiros

Medeiros began his career at age 10, singing for guests on his father’s tour bus on Kauai. Winning the song contest helped him catch the attention of a Phoenix radio executive who was vacationing in Hawaii. When the executive returned stateside, he took the song with him, and it created enough buzz to earn Medeiros his first nationwide deal, with MCA, including a self-titled album pinned on hopes that the adolescent crooner would become the next poster boy to make young girls scream.

And for a while he did, especially in the U.S., where Medeiros’ reedy-voiced cover reached No. 12 on the Billboard Hot 100 in 1987. The accompanying music video that launched this nearly one-hit wonder reflects a hot young man at the height of synth-filled, if cringeworthy, ’80s pop. “The production was surely the very epitome of cheesy and naff,” writes longtime music columnist James Masterton, author of Top 40 Annual 1988.

While a few of Medeiros’ songs became hits, critics were less than impressed. “Teen idols don’t usually last beyond their brief musical moment,” notes Barry Drake, a rock ’n’ roll historian. Duets with budding French pop star Elsa Lunghini and R&B legend Bobby Brown got some attention, with the latter, She Ain’t Worth It, rising to No. 1 in the U.S. in 1990. But Medeiros suffered one of the most humiliating episodes of British TV history on the review program Juke Box Jury that same year. Unaware that the young artist was watching backstage, panelists ripped into his duet with Ray Parker Jr., All I’m Missing Is You. One panelist said he “didn’t like it at all,” another called it “a mess” and the last criticized Medeiros’ dance moves, complaining that he was trying to emulate Bobby Brown … and missing the beat, which made things awkward when Medeiros walked briefly onstage.

Today, Medeiros says his critics were somewhat justified, and he admits that he sold out when he went from singing sappy love tunes to hip-hop. “It was either do that record or not have a way to make a living,” Medeiros tells OZY. While he loved singing, the small-island teen didn’t enjoy the lifestyle or being shuttled from city to city. He could also see that it was the end of the Lionel Richie era of love-ballad singers making it big. “I didn’t see myself being able to be successful anymore as a singer in [that] kind of environment,” he says. This led to some introspection and his return, in 1994, to Hawaii to attend college.

Inspired by his fourth-grade music teacher, Medeiros earned his bachelor’s in history before becoming an educator himself. Before long, he was teaching students whose moms had once been part of his shrieking fandom, and he never looked back. “Education, for me, was a better fit,” he says, because it allows him to spend time with his wife and children. These days, Medeiros’ life is more Principal Rooney than Ferris Bueller. Last April, he was appointed principal of St. Louis School, an all-boys Catholic prep school in Honolulu, just a year after earning his doctorate in education from the University of Southern California.

While the tune that pushed Medeiros into the spotlight saw him telling a girl, “I don’t want to live without you,” he would soon learn that he could live without the fame. He looks back on his teenage years as a time for having friends and falling in love. “There’s not a lot of sophistication there,” he says of his younger self, “and that’s OK.”